Naming Nitriles

That is, nitriles are a class or category of chemical compounds that include a nitrogen atom connected to a carbon atom by a triple covalent bond.

Nitrile molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms.

Names of Nitriles in General

Many chemicals and categories of chemicals have been known by different (general, and specific) names in the past.

Nitriles used to be known as cyanides.

This page indicates the modern names, chemical structures, and some of the previous and less common names of some simple nitriles. It is useful to know and recognise previous and unusual names of nitriles but when naming nitriles in coursework and exam questions the modern names of nitriles are generally expected.

The smallest chemical whose molecular structure includes a nitrogen atom connected to a carbon atom by a triple covalent bond is hydrogen cyanide (HCN), whose structure may be drawn as simply: H-C≡N .
However, because HCN does not include a carbon chain (of at least two carbon atoms linked together) it does not always count as a true 'organic molecule'. Therefore lists of linear nitriles usually start with ethanenitrile, as below.

Names and Structures of simple Linear Nitriles

The homologous series of simple linear nitriles with the -nitrile group (i.e. a single nitrogen atom attached to a carbon atom by a triple covalent bond) attached to the first (=last) carbon atom is shown below for carbon chain lengths of up to 10 carbon atoms:

Carbon atoms in chain

Name

and simple formula

Simple Structure

showing bond types but not accurate bond angles

Previous / Other Names*Examples; not complete lists(Not required for A-Level)

2

ethanenitrile

CH3CN

Acetonitrile

Cyanomethane

Methyl cyanide

Ethanenitrile

Ethyl nitrile

Methanecarbonitrile

Acetonitril

Ethanonitrile

Methylkyanid

Ethane nitrile

3

propanenitrile

CH3CH2CN

n-Propanenitrile

Ethyl cyanide

Propionitrile

Propiononitrile

Propylnitrile

Cyanoethane

Hydrocyanic ether

Propionic nitrile

Ethylkyanid

Propannitril

4

butanenitrile

CH3CH2CH2CN

n-Butanenitrile

Butyronitrile

n-Butyronitrile

Propyl cyanide

n-Propyl cyanide

Butyrylonitrile

1-Cyanopropane

Butane nitrile

Propylkyanid

Butyric acid nitrile

5

pentanenitrile

CH3CH2CH2CH2CN

n-Pentanenitrile

Butyl cyanide

1-Butyl cyanide

Valeronitrile

n-Valeronitrile

1-Cyanobutane

6

hexanenitrile

CH3CH2CH2CH2CH2CN

Hexanonitrile

Capronitrile

n-Capronitrile

Tricapronile

Pentyl cyanide

1-Cyanopentane

Amyl Cyanide

n-Amyl cyanide

7

heptanenitrile

CH3CH2CH2CH2CH2CH2CN

n-Heptanenitrile

Heptanonitrile

Hexyl cyanide

Enanthonitrile

1-Cyanohexane

Heptane nitrile

Heptane-1-nitrile

8

octanenitrile

CH3CH2CH2CH2CH2CH2CH2CN

Heptyl cyanide

Octanonitrile

Caprylonitrile

Caprylnitrile

Arneel 8

1-Cyanoheptane

9

nonanenitrile

CH3CH2CH2CH2CH2CH2CH2CH2CN

Nonanitrile

Nonanonitrile

n-Octyl cyanide

n-Nonanonitrile

n-Octylcyanide

Octyl cyanide

1-Cyanooctane

n-Nonanenitrile

10

decanenitrile

CH3CH2CH2CH2CH2CH2CH2CH2CH2CN

n-Decanenitrile

Nonyl cyanide

Caprinitrile

Decanonitrile

1-Cyanononane

Ethanenitrile ( 2 carbon atoms in chain )

Simple Formula:

CH3CN

Simple Structure:

*Examples of other / previous names:

Acetonitrile

Cyanomethane

Methyl cyanide

Ethanenitrile

Ethyl nitrile

Methanecarbonitrile

Acetonitril

Ethanonitrile

Methylkyanid

Ethane nitrile

Propanenitrile ( 3 carbon atoms in chain )

Simple Formula:

CH3CH2CN

Simple Structure:

*Examples of other / previous names:

n-Propanenitrile

Ethyl cyanide

Propionitrile

Propiononitrile

Propylnitrile

Cyanoethane

Hydrocyanic ether

Propionic nitrile

Ethylkyanid

Propannitril

Butanenitrile ( 4 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CN

Simple Structure:

*Examples of other / previous names:

n-Butanenitrile

Butyronitrile

n-Butyronitrile

Propyl cyanide

n-Propyl cyanide

Butyrylonitrile

1-Cyanopropane

Butane nitrile

Propylkyanid

Butyric acid nitrile

Pentanenitrile ( 5 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CH2CN

Simple Structure:

*Examples of other / previous names:

n-Pentanenitrile

Butyl cyanide

1-Butyl cyanide

Valeronitrile

n-Valeronitrile

1-Cyanobutane

Hexanenitrile ( 6 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CH2CH2CN

Simple Structure:

*Examples of other / previous names:

Hexanonitrile

Capronitrile

n-Capronitrile

Tricapronile

Pentyl cyanide

1-Cyanopentane

Amyl Cyanide

n-Amyl cyanide

Heptanenitrile ( 7 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CH2CH2CH2CN

Simple Structure:

*Examples of other / previous names:

n-Heptanenitrile

Heptanonitrile

Hexyl cyanide

Enanthonitrile

1-Cyanohexane

Heptane nitrile

Heptane-1-nitrile

Octanenitrile ( 8 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2CN

Simple Structure:

*Examples of other / previous names:

Heptyl cyanide

Octanonitrile

Caprylonitrile

Caprylnitrile

Arneel 8

1-Cyanoheptane

Nonanenitrile ( 9 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2CH2CN

Simple Structure:

*Examples of other / previous names:

Nonanitrile

Nonanonitrile

n-Octyl cyanide

n-Nonanonitrile

n-Octylcyanide

Octyl cyanide

1-Cyanooctane

n-Nonanenitrile

Decanenitrile ( 10 carbon atoms in chain )

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2CH2CH2CN

Simple Structure:

*Examples of other / previous names:

n-Decanenitrile

Nonyl cyanide

Caprinitrile

Decanonitrile

1-Cyanononane

Why stop at ten carbon atoms (in the chain) ? It doesn't ... there are more similar linear nitriles. We stopped here due to page width.

Important Note: *The synonyms indicated for compounds listed above are just some examples of alternative names found online and believed to have been used to refer to the substance indicated. They have not all been verified and may include common (non-scientific) names, trade names specific to particular suppliers, and perhaps errors. The purpose of these lists is to give a general indication of the range of names by which nitriles are known - both generally, and specifically.

According to the International Union of Pure and Applied Chemistry (IUPAC) recommendations for nomenclature of organic chemistry, compounds with the general structure -C≡N are called nitriles (and sometimes cyanides) and may be named substitutively in a manner similar to that for acids and other related compounds, see more about naming nitriles at http://www.acdlabs.com/iupac/nomenclature/93/r93_557.htm.